How to Be Carefree

One of the greatest luxuries in life is to not have to worry. This isn’t possible for all people at all times, but there are things all of us can do to be more carefree, especially those of us who have only “first world problems”.

Be very deliberate about taking on obligations. The obvious example is debt, which I talk about all the time. Most people make debt decisions based on their current situation, and not an evaluation of all reasonable outcomes over the term of the loan. Rather than worrying about the debt before they assume it, they are forced to worry about it over the term of the loan. And of course if something happens, it’s even harder to be carefree.

Obligations extend beyond finances, though. Everything you purchase, especially large purchases, comes with some obligation. For example, with all of the properties I’ve bought with my friends, I’m essentially always on call to deal with them. More than once I’ve gotten an email from our Hungarian accountant saying, “You really need to come here by the end of the month to sign a document.” Those obligations are worth it to me, and I can remain carefree and deal with them only because I’ve been judicious about taking on other obligations.

Don’t totally avoid obligations, just make sure that the benefit accrued from them justifies the obligation.

It’s always worth working as hard as you can for things to turn out well, but it’s not worth worrying about if they don’t. If you have the habit of making the best of setbacks, you’ll often find that some of the best things that happen to you stem from the worst. Even COVID, which massively disrupted my life, my business, and my wife’s career, has been overall positive and I would prefer to be where I am today than where I would be if it didn’t happen. Aim for best case scenarios, but don’t assume that worst case scenarios are all that bad.

These days when bad things happen to me I just think, “It will be interesting to see how this turns out”, and usually the result is good. I sometimes take it as a challenge, refusing to let something bad remain bad, and instead thinking, “What would it take for me to be glad that this happened?”

Even if we minimize obligations and recognize that things will go wrong but may end up good anyway, we all have things on our minds that we worry about or wonder about. However, we all also have a ton of things that are going great in our lives and things that have happened that are positive. Focusing on these positive things doesn’t eliminate worry, but it helps put it in context.

Focusing on positives and gratitude can change a mindset of constant worry to one of, “Wow, my life is so great and so many good things are happening that even if a few things coming up don’t go my way, my life is still going to be great.” As a carefree person, that’s generally what I’m thinking.

It seems that sometimes people worry because it’s part of their identity and it makes them feel safe. If they are constantly worrying, nothing will slip by them! Of course, the real effect is that they create problems that don’t exist.

It feels great to be carefree and it feels great to be around carefree people. Keep your obligations small, accept that not everything will go your way, realize that “bad” events often lead to the biggest wins, appreciate all the things that have gone will, and let go of your worrying identity.


Picture is a crazy skull art thing at Area 15 in Las Vegas






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